US20160046621A1 - Indoloacridine-containing derivative, preparation process and use thereof, and organic luminescent device - Google Patents
Indoloacridine-containing derivative, preparation process and use thereof, and organic luminescent device Download PDFInfo
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- US20160046621A1 US20160046621A1 US14/425,254 US201414425254A US2016046621A1 US 20160046621 A1 US20160046621 A1 US 20160046621A1 US 201414425254 A US201414425254 A US 201414425254A US 2016046621 A1 US2016046621 A1 US 2016046621A1
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- United States
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- compound represented
- indoloacridine
- compound
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- PWGAMUODYKBQLG-UHFFFAOYSA-N N1C2=CC=C[CH]C2=CC2=C1C=CC1=NC3=CC=CC=C3[C]21 Chemical compound N1C2=CC=C[CH]C2=CC2=C1C=CC1=NC3=CC=CC=C3[C]21 PWGAMUODYKBQLG-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 150
- 239000000463 material Substances 0.000 claims abstract description 35
- -1 biphenylyl group Chemical group 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 110
- 239000007787 solid Substances 0.000 claims description 82
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 58
- 238000010992 reflux Methods 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 37
- 238000004440 column chromatography Methods 0.000 claims description 32
- 238000001914 filtration Methods 0.000 claims description 32
- 238000000605 extraction Methods 0.000 claims description 29
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 29
- 238000001953 recrystallisation Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 claims description 5
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 5
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 5
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 228
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
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- 239000012153 distilled water Substances 0.000 description 79
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 52
- 229910001873 dinitrogen Inorganic materials 0.000 description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- SMOWFWITUWQSGO-UHFFFAOYSA-N CC1(C2=C3C(CC=C2NC=2C=CC=CC1=2)=NC=1C=CC=CC=13)C Chemical compound CC1(C2=C3C(CC=C2NC=2C=CC=CC1=2)=NC=1C=CC=CC=13)C SMOWFWITUWQSGO-UHFFFAOYSA-N 0.000 description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 31
- 239000012044 organic layer Substances 0.000 description 29
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
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- 230000000052 comparative effect Effects 0.000 description 13
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- 230000005281 excited state Effects 0.000 description 7
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 7
- UDLVBAKTBXFAPP-UHFFFAOYSA-N ClC1=NC2=NC=CN=C2C(=N1)I Chemical compound ClC1=NC2=NC=CN=C2C(=N1)I UDLVBAKTBXFAPP-UHFFFAOYSA-N 0.000 description 6
- CUOJXMPKCMWQEJ-UHFFFAOYSA-N ClC=1N=C(C2=C(N=1)N=CC=C2)I Chemical compound ClC=1N=C(C2=C(N=1)N=CC=C2)I CUOJXMPKCMWQEJ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HZDJFEDYGBOZHE-UHFFFAOYSA-N ClC1=NC2=CC=CC=C2C(=C1)I Chemical compound ClC1=NC2=CC=CC=C2C(=C1)I HZDJFEDYGBOZHE-UHFFFAOYSA-N 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- DCMWJXWYTURQIM-UHFFFAOYSA-N naphthalen-2-yloxyboronic acid Chemical compound C1=CC=CC2=CC(OB(O)O)=CC=C21 DCMWJXWYTURQIM-UHFFFAOYSA-N 0.000 description 5
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- JLFRMMLHHOZVRI-UHFFFAOYSA-N (3-phenylphenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(C=2C=CC=CC=2)=C1 JLFRMMLHHOZVRI-UHFFFAOYSA-N 0.000 description 4
- MBYOBTPZNDJPCC-UHFFFAOYSA-N (4-phenylphenoxy)boronic acid Chemical compound C1=CC(OB(O)O)=CC=C1C1=CC=CC=C1 MBYOBTPZNDJPCC-UHFFFAOYSA-N 0.000 description 4
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H01L51/0067—
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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- H01L51/5016—
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
Definitions
- the disclosure relates to the field of organic photoelectric materials, especially, to an indoloacridine-containing derivative, the preparation process and use thereof, and an organic luminescent device.
- organic electroluminescent (EL) device (hereinafter, briefly referred to as “organic EL device”) is generally composed of two opposite electrodes and at least one layer of an organic light-emitting compound inserted between these two electrodes. Electric charges are injected into the organic layer formed between the anode and the cathode to form electron hole pairs, so that the organic compound having fluorescent or phosphorescent characteristics generates light emission.
- the hole mobility is significantly higher than the electron mobility, so holes and electrons can be more effectively transported to the light-emitting layer when a hole transport layer and an electron transport layer are properly used. Additionally, when a balance between the hole density and the electron density in the light-emitting layer is achieved, the luminous efficiency can be improved.
- the phosphorescence host luminescent materials such as the carbazole ring compounds (e.g. CBP, etc.), and the phosphorescence guest luminescent materials such as a compound attached with iridium (Ir), platinum (Pt) or the like as a central metal atom, are widely used.
- the carbazole ring compounds e.g. CBP, etc.
- the phosphorescence guest luminescent materials such as a compound attached with iridium (Ir), platinum (Pt) or the like as a central metal atom
- the disclosure is to solve the ultimate technical problem, and provides a compound which may be used as a host material for red phosphorescence, a hole-injecting material or a hole-transporting material.
- the compound has an improved electrical stability, a better charge-transporting capability, a high glass transition temperature and does not crystallize.
- the material can be used for producing an organic electroluminescent (EL) device comprising an indoloacridine-containing derivative which has a high efficiency, a high luminance, a long lifetime and a high stability
- the disclosure further provides an organic electroluminescent (EL) device comprising the compound of the disclosure which has a low voltage, a high efficiency, a high luminance, a long lifetime and a high stability.
- the present disclosure provides an indoloacridine-containing derivative represented by formula (I):
- A is a quinoline derivative group-containing compound represented by formula (II):
- X, Y, Z and W represent a carbon atom or a nitrogen atom, and at least one of W, X, Y and Z represents a nitrogen atom;
- R represents a phenyl group, a biphenylyl group, a naphthyl group or a phenanthryl group.
- X represents a nitrogen atom. More preferably, X and Y represent a nitrogen atom. Even more preferably, X, Y and Z represent a nitrogen atom. Still more preferably, X, Y, Z and W represent a nitrogen atom.
- R represents phenyl, 1-naphthyl, 2-naphthyl, 4-biphenylyl, 3-biphenylyl or 9-phenanthryl.
- a preferable example of the organic electroluminescent material in the disclosure which is an indoloacridine-containing derivative, is any one selected from the compounds represented by the formulae 1-24 in the following Table 1.
- the disclosure further provides a process for preparing the indoloacridine-containing derivative represented by formula (I), comprising a step of reacting a compound represented by formula (III)
- R, X, Y, Z and W have the same definitions as those in formula (II).
- the production process includes the following Steps S1 to S3:
- Step S1 adding the compound represented by formula (III), the compound represented by formula (IV), potassium hydroxide, copper iodide and a solvent into a degassed reaction container;
- Step S2 increasing the reaction temperature and refluxing, allowing the reaction to be carried out sufficiently;
- Step S3 performing filtration, washing and recrystallization to obtain the compound represented by formula (I).
- the compound represented by formula (III) is 13,13-dimethyl-7,13-dihydro-5H-indoloacridine.
- the process for producing the compound represented by formula (I) may comprise performing the following Steps M1 to M5 to produce the compound represented by formula (III):
- Step M1 reacting 9,10-dihydro-9,9-dimethylacridine with solid triphosgene to obtain a compound represented by formula (V):
- Step M2 reacting the compound represented by formula (V) with N-bromosuccinimide to obtain a compound represented by formula (VI):
- Step M3 reacting the compound represented by formula (VI) with 2-chloroaniline to obtain a compound represented by formula (VII):
- Step M4 reacting the compound represented by formula (VII) in the presence of palladium acetate, di-tert-butyl methylphosphonium tetraphenylborate and cesium carbonate, to obtain a compound represented by formula (VIII):
- Step M5 removing the chloroformyl protection of the compound represented by formula (VIII) to obtain the compound represented by formula (III).
- the process for preparing the compound represented by formula (I) may comprise producing the compound represented by formula (IV) by reacting R—B(OH) 2 with a compound represented by formula (IX):
- the compound represented by formula (IV) is obtained by the following Steps N1 to N3:
- Step N1 adding the compound represented by formula (IX), R—B(OH) 2 , potassium carbonate and a solvent into a degassed reaction container;
- Step N2 refluxing, allowing the reaction to be carried out sufficiently;
- Step N3 obtaining the compound represented by formula (IV) by performing extraction, washing, drying and purification with column chromatography. This compound can be directly used for producing the compound represented by formula (I).
- the disclosure further provides an organic electroluminescent device, comprising a first electrode, a second electrode and one or more organic compound layer(s) provided between the first electrode and the second electrode, wherein at least one organic compound layer comprises at least one compound represented by formula (I).
- the compound represented by formula (I) is a phosphorescence host material.
- the disclosure further provides use of the compound represented by formula (I) as a phosphorescence host material, a hole-injecting material or a hole-transporting material in an organic electroluminescent device.
- the disclosure provides an indoloacridine-containing derivative, the preparation process and its use in an organic electroluminescent device.
- the indoloacridine-containing derivative has high luminescence efficiency. High luminescence efficiency indicates that the compound can be used as a luminescent material or a luminescent host material, especially as a red phosphorescence host material used in an organic electroluminescent device. It has a high glass transition temperature and does not crystallize easily.
- the organic electroluminescent device using the indoloacridine-containing derivative exhibits a high efficiency, a high luminance, a long lifetime, and has the advantage of lower manufacturing cost. Additionally, the lifetime of the organic electroluminescent device is prolonged and the manufacturing cost of the organic electroluminescent device is reduced.
- the present disclosure provides an indoloacridine-containing derivative represented by formula (I):
- A is a quinoline derivative group-containing compound represented by formula (II):
- X, Y, Z and W represent a carbon atom or a nitrogen atom, and at least one of W, X, Y and Z represents a nitrogen atom;
- R represents a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group.
- X represents a nitrogen atom. More preferably, X and Y represent a nitrogen atom. Even more preferably, X, Y and Z represent a nitrogen atom. Still more preferably, X, Y, Z and W represent a nitrogen atom.
- R represents phenyl, 1-naphthyl, 2-naphthyl, 4-biphenylyl, 3-biphenylyl or 9-phenanthryl.
- organic electroluminescent material in the disclosure which is an indoloacridine-containing derivative, is any one selected from the compounds represented by the formulae 1-24 in the following Table 1:
- the disclosure further provides a process for preparing the indoloacridine-containing derivative represented by formula (I), comprising a step of reacting a compound represented by formula (III)
- R, X, Y, Z and W have the same definitions as those in formula (II).
- the production process includes the following Steps S1 to S3:
- Step S1 adding the compound represented by formula (III), the compound represented by formula (IV), potassium hydroxide, copper iodide and a solvent into a degassed reaction container;
- Step S2 increasing the reaction temperature and refluxing, allowing the reaction to be carried out sufficiently;
- Step S3 performing filtration, washing and recrystallization to obtain the compound represented by formula (I).
- the compound represented by formula (IV), the compound represented by formula (III), copper iodide, potassium hydroxide, 8-hydroxylquinoline and dimethyl sulfoxide are heated and stirred under nitrogen atmosphere. After the reaction has been completed, methanol is added thereto at normal temperature. After filtration, washing and recrystallization are performed, the indoloacridine-containing derivative represented by formula (I) is obtained.
- the compound represented by formula (III) is 13,13-dimethyl-7,13-dihydro-5H-indoloacridine.
- the process for producing the compound represented by formula (I) may comprise performing the following Steps M1 to M5 to produce the compound represented by formula (III):
- Step M1 reacting 9,10-dihydro-9,9-dimethylacridine with solid triphosgene to obtain a dimethylacridine compound protected by chloroformyl, which is represented by formula (V):
- Step M2 reacting the compound represented by formula (V) with N-bromosuccinimide to obtain a dimethylacridine bromide protected by chloroformyl, which is represented by formula (VI):
- Step M3 reacting the compound represented by formula (VI) with 2-chloroaniline to obtain a chlorophenyl dimethylacridineamine compound protected by chloroformyl, which is represented by formula (VII):
- Step M4 reacting the compound represented by formula (VII) in the presence of palladium acetate, di-tert-butyl methylphosphonium tetraphenylborate and cesium carbonate, to obtain a dimethylacridinoindole compound protected by chloroformyl, which is represented by formula (VIII):
- Step M5 removing the chloroformyl protection of the compound represented by formula (VIII) to obtain the compound 13,13-dimethyl-7,13-dihydro-5H-indoloacridine represented by formula (III).
- step M1 adding 9,10-dihydro-9,9-dimethylacridine, solid triphosgene and toluene into a reaction container, heating them to reflux, and performing washing, filtration and drying after the reaction is completed to obtain the compound represented by formula (V);
- step M2 dissolving the compound represented by formula (V) in a solvent, adding a solution of N-bromosuccinimide under stirring at 0° C., and performing washing, drying and purification after the reaction is completed to obtain the compound represented by formula (VI);
- step M3 dissolving the above-mentioned compound represented by formula (VI), along with 2-chloroaniline, palladium acetate, tri-tert-butylphosphine and cesium carbonate, in a solvent, stirring them at 120° C., allowing the reaction to be carried out sufficiently, and then performing washing, drying and purification to obtain the compound represented by formula (VII);
- step M4 dissolving the compound represented by formula (VII), along with palladium acetate, di-tert-butylmethylphorsphonium tetraphenylborate and cesium carbonate, in a solvent, allowing the reaction to be carried out sufficiently at 190° C., and then performing washing, drying and purification to obtain the compound represented by formula (VIII);
- step M5 dissolving the compound represented by formula (VIII), along with sodium hydroxide and isopropanol, in a solvent, allowing the reaction to be carried out sufficiently at 40° C. under reflux, and then performing suction filtration and drying, to obtain 13,13-dimethyl-7,13-dihydro-5H-indoloacridine.
- the process for preparing the compound represented by formula (I) may comprise producing the compound represented by formula (IV) by reacting R—B(OH) 2 with the compound represented by formula (IX):
- the compound represented by formula (IV) is obtained by the following Steps N1 to N3:
- Step N1 adding the compound represented by formula (IX), R—B(OH) 2 , potassium carbonate and a solvent into a degassed reaction container;
- Step N2 refluxing, allowing the reaction to be carried out sufficiently;
- Step N3 obtaining the compound represented by formula (IV) by performing extraction, washing, drying and purification with column chromatography. This compound can be directly used for producing the compound represented by formula (I).
- the compound represented by formula (IX) and a boric acid having an R substituent are dissolved in toluene. Tetrakis(triphenylphosphine)palladium, potassium carbonate and distilled water are added therein under nitrogen protection. The mixture is stirred under reflux to perform reaction. After the reaction has been completed, the quinazoline having an R substituent is obtained by performing extraction, drying, filtration, distillation under reduced pressure and column chromatography.
- indoloacridine-containing derivatives are produced by the following process: reacting 2-chloro-4-iodoquinazoline with a boric acid having an R substituent to produce a chloride of quinazoline having an R substituent; further reacting the chloride of quinazoline having an R substituent with 13,13-dimethyl-7,13-dihydro-5H-indoloacridine to obtain an indoloacridine-containing derivative.
- the specific synthesis route is as follows:
- the indoloacridine-containing derivatives of the present disclosure can be obtained, by using various compounds represented by formula (IX) to replace 2-chloro-4-iodoquinazoline in the above route.
- the compound 9 also can be synthesized by following process. This process was applicable for synthesizing compounds 1-8 and 10-24, too.
- Organic electroluminescent devices were prepared by using the compounds 1-24 prepared from the above preparation examples, and then compared with the comparative sample.
- the compound of formula (I) can be used as a red phosphorescence host material, a hole-injecting material or a hole-transporting material. The disclosure was illustrated below by using the compound as a red phosphorescence host material.
- An organic electroluminescent device having the following structure was prepared by using a compound of chemical formula a as a luminescent host material, a compound of chemical formula b as a doping material, 2-TNATA (4,4,4-tri(N-naphthyl)-N-phenylamino)-triphenylamine) represented by chemical formula c as a hole-injecting material, and ⁇ -NPD (N,N′-di(naphthyl)-N,N′-diphenylbenzidine) represented by chemical formula d as a hole-transporting material:
- a 15 ⁇ /cm 2 (1000 ⁇ ) ITO glass substrate from Corning Co. was cut into a size of 50 mm*50 mm*0.7 mm, and then under the irradiation of microwave, washed in acetone, isopropanol, purified water in turn for 15 minutes respectively, and then further washed in UV for 30 minutes.
- a hole injection layer was formed by vacuum depositing 2-TNATA to a thickness of 80 nm on the substrate.
- a hole transport layer was formed by vacuum depositing ⁇ -NPD to a thickness of 30 nm on the hole injection layer.
- a light-emitting layer was formed by vacuum depositing a compound represented by chemical formula a and a compound represented by chemical formula b (at a doping ratio of 8%) to a thickness of 30 nm on the hole transport layer.
- An electron transport layer was formed by vacuum depositing Alg 3 to a thickness of 30 nm on the light-emitting layer.
- 0.5 nm LiF (electron injection) and 60 nm Al were vacuum depositing in turn, thereby an organic luminescent device was produced.
- vacuum deposition was carried out by using an EL deposition machine manufactured by DOV Co., Korean.
- the organic luminescent devices having following structures were produced by using the process in comparative example 1, with the exception that the compounds 1 to 24 shown in the preparation examples were used as the light-emitting layer compound instead of the compound a.
- the organic luminescent devices having the structure of ITO/2-TNATA (80 nm)/ ⁇ -NPD (30 nm)/indoloacridine-containing derivatives 1 to 24+compound b] (25 nm, content of b therein being 8.0%)/Alq 3 (30 nm)/LiF(0.5 nm)/Al(60 nm).
- the comparative sample and the samples 1 to 24 were tested for evaluating the driving voltage, luminance, luminous efficiency and luminous color by using Keithley 2400 series digital source apparatus from the Taiwan Branch of American Keithley Instruments Inc., konica minolta CS-2000 from Konica Minolta, and CS-2000A photometer.
- the comparative sample and the samples 1 to 24 were subjected to the same tests. The results were listed in Table 3:
- the lights emitted from the samples mentioned above were in a wavelength range of from 632 to 640 nm, showing a color of red.
- the samples of the application examples 1 to 24 had significantly higher luminous efficiency.
- a lifetime testing apparatus LTS-1004AC of ENC Co. was used for the samples produced in the above-mentioned comparative example 1 and application examples 1 to 24, wherein lifetime of each sample was measured when 97% was reached by using 3000 nit as the standard. The results were shown in Table 4.
- organic luminescent devices having a structure of ITO/2-TNATA (80 nm)+indoloacridine-containing derivatives 1 to 24/ ⁇ -NPD (30 nm)/compound a (30 nm, where b content was 8%)/Alg 3 (30 nm)/LiF (0.5 nm)/Al (60 nm) were prepared by using the process of comparative example 1, with the exception that the compounds 1 to 24 shown in the preparation examples were used as a hole injection material instead of the compound c. That is, these compounds 1-24 may be used as a hole-injecting material.
- Organic luminescent devices having a structure of ITO/2-TNATA (80 nm)/indoloacridine-containing derivatives 1 to 24+ ⁇ -NPD (30 nm)/compound a+compound b (25 nm, where b content was 8.0%)/Alq 3 (30 nm)/LiF (0.5 nm)/Al (60 nm) were prepared by using the process of comparative example 1, with the exception that the compounds 1 to 24 shown in the preparation examples, which may used as a hole-transporting material, were used for the compound for the hole transporting layer instead of the compound d.
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Abstract
Description
- The disclosure relates to the field of organic photoelectric materials, especially, to an indoloacridine-containing derivative, the preparation process and use thereof, and an organic luminescent device.
- An organic electroluminescent (EL) device (hereinafter, briefly referred to as “organic EL device”) is generally composed of two opposite electrodes and at least one layer of an organic light-emitting compound inserted between these two electrodes. Electric charges are injected into the organic layer formed between the anode and the cathode to form electron hole pairs, so that the organic compound having fluorescent or phosphorescent characteristics generates light emission.
- The research on the organic EL material started from 1950, beginning with the observation of Bernanose on an organic pigment-containing polymeric thin film to which high current and voltage was applied. In 1965, Pope et al. for the first time discovered the electroluminescent property of anthracene single crystal, which is the first example of the electroluminescence of organic compounds. In 1987, Tang et al. from Kodak Company discovered that even at a low voltage of 10V or less, an organic luminescent device, which is formed from an organic material and has laminated separate functional layers, can provide a high luminance of 1000 cd/cm2 or more.
- In an organic material, the hole mobility is significantly higher than the electron mobility, so holes and electrons can be more effectively transported to the light-emitting layer when a hole transport layer and an electron transport layer are properly used. Additionally, when a balance between the hole density and the electron density in the light-emitting layer is achieved, the luminous efficiency can be improved.
- When an electron and a hole recombine in an organic molecule, due to different manners of electron spin symmetry, two forms of excited state will occur. One is the form of a singlet excited state formed by a ground state electron with asymmetric spin, which releases energy in the form of fluorescence and then returns to the ground state; the other is the form of a triplet excited state formed by a ground state electron with symmetric spin, which releases energy in the form of phosphorescence and then returns to the ground state. According to theoretical speculation, the ratio of the singlet excited state to the triplet excited state caused by the recombination of electric charges is 1:3. If the energy of the singlet excited state is transferred to the triplet excited state for emitting phosphorescence, the internal quantum efficiency thereby may be close to 100%.
- Generally, the phosphorescence host luminescent materials such as the carbazole ring compounds (e.g. CBP, etc.), and the phosphorescence guest luminescent materials such as a compound attached with iridium (Ir), platinum (Pt) or the like as a central metal atom, are widely used.
- The disclosure is to solve the ultimate technical problem, and provides a compound which may be used as a host material for red phosphorescence, a hole-injecting material or a hole-transporting material. The compound has an improved electrical stability, a better charge-transporting capability, a high glass transition temperature and does not crystallize. The material can be used for producing an organic electroluminescent (EL) device comprising an indoloacridine-containing derivative which has a high efficiency, a high luminance, a long lifetime and a high stability The disclosure further provides an organic electroluminescent (EL) device comprising the compound of the disclosure which has a low voltage, a high efficiency, a high luminance, a long lifetime and a high stability.
- The present disclosure provides an indoloacridine-containing derivative represented by formula (I):
- wherein A is a quinoline derivative group-containing compound represented by formula (II):
- wherein X, Y, Z and W represent a carbon atom or a nitrogen atom, and at least one of W, X, Y and Z represents a nitrogen atom; R represents a phenyl group, a biphenylyl group, a naphthyl group or a phenanthryl group. Preferably, X represents a nitrogen atom. More preferably, X and Y represent a nitrogen atom. Even more preferably, X, Y and Z represent a nitrogen atom. Still more preferably, X, Y, Z and W represent a nitrogen atom. Preferably, R represents phenyl, 1-naphthyl, 2-naphthyl, 4-biphenylyl, 3-biphenylyl or 9-phenanthryl.
- A preferable example of the organic electroluminescent material in the disclosure, which is an indoloacridine-containing derivative, is any one selected from the compounds represented by the formulae 1-24 in the following Table 1.
- The disclosure further provides a process for preparing the indoloacridine-containing derivative represented by formula (I), comprising a step of reacting a compound represented by formula (III)
- with a compound represented by formula (IV)
- wherein R, X, Y, Z and W have the same definitions as those in formula (II).
- Preferably, the production process includes the following Steps S1 to S3:
- Step S1: adding the compound represented by formula (III), the compound represented by formula (IV), potassium hydroxide, copper iodide and a solvent into a degassed reaction container;
- Step S2: increasing the reaction temperature and refluxing, allowing the reaction to be carried out sufficiently;
- Step S3: performing filtration, washing and recrystallization to obtain the compound represented by formula (I).
- The compound represented by formula (III) is 13,13-dimethyl-7,13-dihydro-5H-indoloacridine.
- The process for producing the compound represented by formula (I) may comprise performing the following Steps M1 to M5 to produce the compound represented by formula (III):
- Step M1: reacting 9,10-dihydro-9,9-dimethylacridine with solid triphosgene to obtain a compound represented by formula (V):
- Step M2: reacting the compound represented by formula (V) with N-bromosuccinimide to obtain a compound represented by formula (VI):
- Step M3: reacting the compound represented by formula (VI) with 2-chloroaniline to obtain a compound represented by formula (VII):
- Step M4: reacting the compound represented by formula (VII) in the presence of palladium acetate, di-tert-butyl methylphosphonium tetraphenylborate and cesium carbonate, to obtain a compound represented by formula (VIII):
- Step M5: removing the chloroformyl protection of the compound represented by formula (VIII) to obtain the compound represented by formula (III).
- The process for preparing the compound represented by formula (I) may comprise producing the compound represented by formula (IV) by reacting R—B(OH)2 with a compound represented by formula (IX):
- Preferably, the compound represented by formula (IV) is obtained by the following Steps N1 to N3:
- Step N1: adding the compound represented by formula (IX), R—B(OH)2, potassium carbonate and a solvent into a degassed reaction container;
- Step N2: refluxing, allowing the reaction to be carried out sufficiently;
- Step N3: obtaining the compound represented by formula (IV) by performing extraction, washing, drying and purification with column chromatography. This compound can be directly used for producing the compound represented by formula (I).
- The disclosure further provides an organic electroluminescent device, comprising a first electrode, a second electrode and one or more organic compound layer(s) provided between the first electrode and the second electrode, wherein at least one organic compound layer comprises at least one compound represented by formula (I). Preferably, the compound represented by formula (I) is a phosphorescence host material.
- The disclosure further provides use of the compound represented by formula (I) as a phosphorescence host material, a hole-injecting material or a hole-transporting material in an organic electroluminescent device.
- The disclosure provides an indoloacridine-containing derivative, the preparation process and its use in an organic electroluminescent device. The indoloacridine-containing derivative has high luminescence efficiency. High luminescence efficiency indicates that the compound can be used as a luminescent material or a luminescent host material, especially as a red phosphorescence host material used in an organic electroluminescent device. It has a high glass transition temperature and does not crystallize easily. The organic electroluminescent device using the indoloacridine-containing derivative exhibits a high efficiency, a high luminance, a long lifetime, and has the advantage of lower manufacturing cost. Additionally, the lifetime of the organic electroluminescent device is prolonged and the manufacturing cost of the organic electroluminescent device is reduced.
- The present disclosure provides an indoloacridine-containing derivative represented by formula (I):
- wherein A is a quinoline derivative group-containing compound represented by formula (II):
- wherein X, Y, Z and W represent a carbon atom or a nitrogen atom, and at least one of W, X, Y and Z represents a nitrogen atom; R represents a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group. Preferably, X represents a nitrogen atom. More preferably, X and Y represent a nitrogen atom. Even more preferably, X, Y and Z represent a nitrogen atom. Still more preferably, X, Y, Z and W represent a nitrogen atom. Preferably, R represents phenyl, 1-naphthyl, 2-naphthyl, 4-biphenylyl, 3-biphenylyl or 9-phenanthryl.
- A preferable example of the organic electroluminescent material in the disclosure, which is an indoloacridine-containing derivative, is any one selected from the compounds represented by the formulae 1-24 in the following Table 1:
- The disclosure further provides a process for preparing the indoloacridine-containing derivative represented by formula (I), comprising a step of reacting a compound represented by formula (III)
- with a compound represented by formula (IV)
- wherein R, X, Y, Z and W have the same definitions as those in formula (II).
- Preferably, the production process includes the following Steps S1 to S3:
- Step S1: adding the compound represented by formula (III), the compound represented by formula (IV), potassium hydroxide, copper iodide and a solvent into a degassed reaction container;
- Step S2: increasing the reaction temperature and refluxing, allowing the reaction to be carried out sufficiently;
- Step S3: performing filtration, washing and recrystallization to obtain the compound represented by formula (I).
- More specifically, the compound represented by formula (IV), the compound represented by formula (III), copper iodide, potassium hydroxide, 8-hydroxylquinoline and dimethyl sulfoxide are heated and stirred under nitrogen atmosphere. After the reaction has been completed, methanol is added thereto at normal temperature. After filtration, washing and recrystallization are performed, the indoloacridine-containing derivative represented by formula (I) is obtained.
- The compound represented by formula (III) is 13,13-dimethyl-7,13-dihydro-5H-indoloacridine.
- The process for producing the compound represented by formula (I) may comprise performing the following Steps M1 to M5 to produce the compound represented by formula (III):
- Step M1: reacting 9,10-dihydro-9,9-dimethylacridine with solid triphosgene to obtain a dimethylacridine compound protected by chloroformyl, which is represented by formula (V):
- Step M2: reacting the compound represented by formula (V) with N-bromosuccinimide to obtain a dimethylacridine bromide protected by chloroformyl, which is represented by formula (VI):
- Step M3: reacting the compound represented by formula (VI) with 2-chloroaniline to obtain a chlorophenyl dimethylacridineamine compound protected by chloroformyl, which is represented by formula (VII):
- Step M4: reacting the compound represented by formula (VII) in the presence of palladium acetate, di-tert-butyl methylphosphonium tetraphenylborate and cesium carbonate, to obtain a dimethylacridinoindole compound protected by chloroformyl, which is represented by formula (VIII):
- Step M5: removing the chloroformyl protection of the compound represented by formula (VIII) to obtain the compound 13,13-dimethyl-7,13-dihydro-5H-indoloacridine represented by formula (III).
- More specifically, the following steps M1 to M5 are performed:
- step M1: adding 9,10-dihydro-9,9-dimethylacridine, solid triphosgene and toluene into a reaction container, heating them to reflux, and performing washing, filtration and drying after the reaction is completed to obtain the compound represented by formula (V);
- step M2: dissolving the compound represented by formula (V) in a solvent, adding a solution of N-bromosuccinimide under stirring at 0° C., and performing washing, drying and purification after the reaction is completed to obtain the compound represented by formula (VI);
- step M3: dissolving the above-mentioned compound represented by formula (VI), along with 2-chloroaniline, palladium acetate, tri-tert-butylphosphine and cesium carbonate, in a solvent, stirring them at 120° C., allowing the reaction to be carried out sufficiently, and then performing washing, drying and purification to obtain the compound represented by formula (VII);
- step M4: dissolving the compound represented by formula (VII), along with palladium acetate, di-tert-butylmethylphorsphonium tetraphenylborate and cesium carbonate, in a solvent, allowing the reaction to be carried out sufficiently at 190° C., and then performing washing, drying and purification to obtain the compound represented by formula (VIII);
- step M5: dissolving the compound represented by formula (VIII), along with sodium hydroxide and isopropanol, in a solvent, allowing the reaction to be carried out sufficiently at 40° C. under reflux, and then performing suction filtration and drying, to obtain 13,13-dimethyl-7,13-dihydro-5H-indoloacridine.
- The process for preparing the compound represented by formula (I) may comprise producing the compound represented by formula (IV) by reacting R—B(OH)2 with the compound represented by formula (IX):
- Preferably, the compound represented by formula (IV) is obtained by the following Steps N1 to N3:
- Step N1: adding the compound represented by formula (IX), R—B(OH)2, potassium carbonate and a solvent into a degassed reaction container;
- Step N2: refluxing, allowing the reaction to be carried out sufficiently;
- Step N3: obtaining the compound represented by formula (IV) by performing extraction, washing, drying and purification with column chromatography. This compound can be directly used for producing the compound represented by formula (I).
- More specifically, the compound represented by formula (IX) and a boric acid having an R substituent are dissolved in toluene. Tetrakis(triphenylphosphine)palladium, potassium carbonate and distilled water are added therein under nitrogen protection. The mixture is stirred under reflux to perform reaction. After the reaction has been completed, the quinazoline having an R substituent is obtained by performing extraction, drying, filtration, distillation under reduced pressure and column chromatography.
- For example, some indoloacridine-containing derivatives are produced by the following process: reacting 2-chloro-4-iodoquinazoline with a boric acid having an R substituent to produce a chloride of quinazoline having an R substituent; further reacting the chloride of quinazoline having an R substituent with 13,13-dimethyl-7,13-dihydro-5H-indoloacridine to obtain an indoloacridine-containing derivative. The specific synthesis route is as follows:
- Similar to the above process, the indoloacridine-containing derivatives of the present disclosure can be obtained, by using various compounds represented by formula (IX) to replace 2-chloro-4-iodoquinazoline in the above route.
- The present disclosure is described in more detail by the following examples. However, the following examples are only to illustrate the present disclosure more specifically, and the scope of the present disclosure is not limited to the examples. According to the user, the following examples may be modified and changed within the scope of the present disclosure.
- Preparation example A: synthesis of the compound represented by formula (III), i.e. 13,13-dimethyl-7,13-dihydro-5H-indoloacridine
- The process for synthesizing 13,13-dimethyl-7,13-dihydro-5H-indoloacridine is as follows.
- Into a 250 ml three-necked flask equipped with a reflux device, 62.78 g (0.30 mol) of the compound represented by formula (IV), 35.6 g (0.12 mol) of solid triphosgene and 500 ml of toluene were charged. The temperature was raised to a reflux temperature. The reaction was carried out under reflux for 10 h. The end point of the reaction was determined by thin-layer chromatography (TLC). After the reaction was ended, the reaction product was cooled to room temperature, filtered by suction and then dried to obtain 61 g of a pale blue solid. The filtrate was concentrated until it was almost dry. 10 ml of petroleum ether were added thereto. Then filtering by suction and drying were performed, so as to obtain 45.81 g of the compound represented by formula (V), which is a dimethylacridine compound protected by chloroformyl, with a yield of 93.0%.
- 45.81 g (0.279 mol) of the compound represented by formula (V) were dissolved in 800 ml of DMF (N,N-dimethyl formamide) and stirred at 0° C. for 10 min. A solution of 49.82 g (0.279 mol) of NBS (N-bromosuccinimide) in 350 ml DMF was added thereto slowly. The mixture was stirred at 0° C. for 6 hours. After the reaction was ended, distilled water and ethyl acetate were added into the mixture. The organic layer was dried over anhydrous MgSO4. The solvent was removed by a rotation evaporator. Then, a column chromatography was performed using ethyl acetate to obtain 82.17 g of the compound of formula (VI), which is a dimethylacridine bromide protected by chloroformyl, with a yield of 84%.
- 82.17 g (0.234 mol) of the compound of formula (VI), 36.28 g (0.281 mol) of 2-chloroaniline, 1.60 g (7.08 mmol) of palladium acetate, 15.55 ml (0.023 mol) of 50% tri-tert-butylphosphine and 154.22 g (0.47 mmol) of cesium carbonate were dissolved in 800 ml of toluene. The reaction was performed by stirring at 120° C. for 4 hours. After the reaction was ended, distilled water and ethyl acetate were added into the mixture. The organic layer was dried over anhydrous MgSO4. The solvent was removed by a rotation evaporator. Then, a column chromatography was performed by using ethyl acetate, so as to obtain 72.51 g of the compound of formula (VII), which is a chlorophenyl dimethylacridineamine compound protected by chloroformyl, with a yield of 78%.
- 72.51 g (0.182 mol) of the compound of formula (VII), 8.34 mg (0.037 mol) of palladium acetate, 18.25 g (0.075 mmol) of di-tert-butyl methylphosphonium tetraphenylborate and cesium carbonate (304.2 g, 0.912 mol) were dissolved in 800 ml of dimethyl acetamide under stirring, and reacted at 190° C. for 4 hours. After the reaction was ended, the mixture was added into distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO4. The solvent was removed by a rotation evaporator. Then, a column chromatography was performed by using ethyl acetate, to obtain 53.19 g of the compound of formula (VIII), which is a dimethylacridinoindole compound protected by chloroformyl, with a yield of 81%.
- 53.19 g (0.147 mol) of the compound of formula (VIII), 17.64 g (0.44 mol) of sodium hydroxide and 300 ml of isopropanol were charged into a 500 ml four-necked flask equipped with a reflux device. The reaction was performed at 40° C. for 3 h. The end point of the reaction was determined by TLC. After the reaction was ended, about 200 ml isopropanol was distilled off under reduced pressure. The pH was adjusted to 12 using a saturated sodium bicarbonate solution. A large amount of solid precipitated. The mixture was stirred for 30 min, followed by suction filtration. The filter cake was washed with 100 ml water. After drying, the yellow compound of formula (III) was obtained, with a yield of 98.2%.
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- 0.10 mol of 2-chloro-4-iodoquinoline and 0.13 mol of phenyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.072 mol of a white solid intermediate 2-chloro-4-(2-phenyl)quinoline was obtained, with a yield of 72%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(2-phenyl)quinoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.036 mol of compound 1, with a yield of 75%.
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- 0.10 mol of 2-chloro-4-iodoquinoline and 0.14 mol of 1-naphthyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.077 mol of a white solid intermediate 2-chloro-4-(1-naphthyl)quinoline was obtained, with a yield of 77%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(1-naphthyl)quinoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0384 mol of compound 2, with a yield of 80%.
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- 0.10 mol of 2-chloro-4-iodoquinoline and 0.12 mol of 2-naphthyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.074 mol of a white solid intermediate 2-chloro-4-(2-naphthyl)quinoline was obtained, with a yield of 74%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(2-naphthyl)quinoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0379 mol of compound 3, with a yield of 79%.
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- 0.10 mol of 2-chloro-4-iodoquinoline and 0.13 mol of 4-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.081 mol of a white solid intermediate 4-([1,1′-biphenyl]-4-yl)-2-chloroquinoline was obtained, with a yield of 81%.
- In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-4-yl)-2-chloroquinoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0341 mol of compound 4, with a yield of 71%.
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- 0.10 mol of 2-chloro-4-iodoquinazoline and 0.14 mol of 3-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.078 mol of a white solid intermediate 4-([1,1′-biphenyl]-3-yl)-2-chloroquinoline was obtained, with a yield of 78%.
- In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-3-yl)-2-chloroquinoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0369 mol of compound 5, with a yield of 77%.
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- 0.10 mol of 2-chloro-4-iodoquinoline and 0.12 mol of 9-phenanthryl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.075 mol of a white solid intermediate 2-chloro-4-(9-phenanthryl)quinoline was obtained, with a yield of 75%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(9-phenanthryl)quinoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0389 mol of compound 6, with a yield of 81%.
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- 0.10 mol of 2-chloro-4-iodoquinazoline and 0.12 mol of phenyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.082 mol of a white solid intermediate 2-chloro-4-(2-phenyl)quinazoline was obtained, with a yield of 82%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(2-phenyl)quinazoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0384 mol of compound 7, with a yield of 80%.
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- 0.10 mol of 2-chloro-4-iodoquinazoline and 0.13 mol of 1-naphthyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.079 mol of a white solid intermediate 2-chloro-4-(2-naphthyl)quinazoline was obtained, with a yield of 79%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(1-naphthyl)quinazoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0350 mol of compound 8, with a yield of 73%.
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- 0.10 mol of 2-chloro-4-iodoquinazoline and 0.12 mol of 2-naphthyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.076 mol of a white solid intermediate 2-chloro-4-(2-naphthyl)quinazoline was obtained, with a yield of 76%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(2-naphthyl)quinazoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0384 mol of compound 9, with a yield of 80%.
- The compound 9 also can be synthesized by following process. This process was applicable for synthesizing compounds 1-8 and 10-24, too.
- Synthesis of Intermediate Compound 9-1
- 29.05 g (0.1 mol) of 2-chloro-4-iodoquinazoline and 20.64 g (0.12 mmol) of 2-naphthyl boric acid were dissolved in 1 L of toluene. 11.7 g (10.15 mol) of tetrakis(triphenylphosphine)palladium, 34.55 g (0.25 mol) of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 22.1 g of a white solid intermediate compound 9-1 was obtained, with a yield of 76%.
- Synthesis of Compound 9
- In nitrogen gas, 13.96 g (0.048 mol) of the intermediate 9-1, 5.97 g (0.02 mol) of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 1.52 g (0.008 mol) of copper iodide, 3.09 g (0.055 mol) of potassium hydroxide, 1.16 g of (0.008 mol) 8-hydroxyquinoline and 100 ml of dimethyl sulfoxide (DMSO) were heated to 150° C. and stirred. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 12.91 g of compound 9, with a yield of 80%.
- The HPLC purity was higher than 99%. Mass Spectrum: the calculated value was 806.95; the measured value was 806.96. Element Analysis: calculated values are C, 84.84%; H, 4.75%; N, 10.41%; measured values are C, 84.83%; H, 4.76%; N, 10.41%.
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- 0.10 mol of 2-chloro-4-iodoquinazoline and 0.12 mol of 4-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.073 mol of a white solid intermediate 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline was obtained, with a yield of 73%.
- In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-4-yl)-2-chloroquinazoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0394 mol of compound 10, with a yield of 82%.
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- 0.10 mol of 2-chloro-4-iodoquinazoline and 0.11 mol of 3-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.078 mol of a white solid intermediate 4-([1,1′-biphenyl]-3-yl)-2-chloroquinazoline was obtained, with a yield of 78%.
- In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-3-yl)-2-chloroquinazoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0355 mol of compound 11, with a yield of 74%.
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- 0.10 mol of 2-chloro-4-iodoquinazoline and 0.12 mol 9-phenanthryl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.073 mol of a white solid intermediate 2-chloro-4-(9-phenanthryl)quinazoline was obtained, with a yield of 73%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(9-phenanthryl)quinazoline, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0340 mol of compound 12, with a yield of 71%.
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- 0.10 mol of 2-chloro-4-iodopyrido[2,3-d]pyrimidine and 0.13 mol of phenyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.074 mol of a white solid intermediate 2-chloro-4-phenylpyrido[2,3-d]pyrimidine was obtained, with a yield of 74%.
- In nitrogen gas, 0.0480 mol of the intermediate 2-chloro-4-phenylpyrido[2,3-d]pyrimidine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0374 mol of compound 13, with a yield of 78%.
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- 0.10 mol of 2-chloro-4-iodopyrido[2,3-d]pyrimidine and 0.12 mol of 1-naphthyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.076 mol of a white solid intermediate 2-chloro-4-(1-naphthyl)pyrido[2,3-d]pyrimidine was obtained, with a yield of 76%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(1-naphthyl)pyrido[2,3-d]pyrimidine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0370 mol of compound 14, with a yield of 77%.
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- 0.10 mol of 2-chloro-4-iodopyrido[2,3-d]pyrimidine and 0.12 mol of 2-naphthyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.076 mol of a white solid intermediate 2-chloro-4-(2-naphthyl)pyrido[2,3-d]pyrimidine was obtained, with a yield of 76%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(2-naphthyl)pyrido[2,3-d]pyrimidine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0370 mol of compound 15, with a yield of 77%.
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- 0.10 mol of 2-chloro-4-iodopyrido[2,3-d]pyrimidine and 0.12 mol of 4-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.0740 mol of a white solid intermediate 4-([1,1′-biphenyl]-4-yl)-2-chloropyrido[2,3-d]pyrimidine was obtained, with a yield of 74%.
- In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-4-yl)-2-chloropyrido[2,3-d]pyrimidine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0374 mol of compound 16, with a yield of 78%.
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- 0.10 mol of 2-chloro-4-iodopyrido[2,3-d]pyrimidine and 0.14 mol of 3-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.0780 mol of a white solid intermediate 4-([1,1′-biphenyl]-3-yl)-2-chloropyrido[2,3-d]pyrimidine was obtained, with a yield of 78%.
- In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-3-yl)-2-chloropyrido[2,3-d]pyrimidine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0379 mol of compound 17, with a yield of 79%.
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- 0.10 mol of 2-chloro-4-iodopyrido[2,3-d]pyrimidine and 0.12 mol of 9-phenanthryl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.076 mol of a white solid intermediate 2-chloro-4-(9-phenanthryl)pyrido[2,3-d]pyrimidine was obtained, with a yield of 76%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(9-phenanthryl)pyrido[2,3-d]pyrimidine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0374 mol of compound 18, with a yield of 78%.
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- 0.10 mol of 2-chloro-4-iodopteridine and 0.13 mol of phenyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.076 mol of a white solid intermediate 2-chloro-4-phenylpteridine was obtained, with a yield of 76%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-phenylpteridine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0374 mol of compound 19, with a yield of 78%.
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- 0.10 mol of 2-chloro-4-iodopteridine and 0.14 mol of 1-naphthyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.074 mol of a white solid intermediate 2-chloro-4-(1-naphthyl)pteridine was obtained, with a yield of 74%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(1-naphthyl)pteridine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0365 mol of compound 20, with a yield of 76%.
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- 0.10 mol of 2-chloro-4-iodopteridine and 0.13 mol of 2-naphthyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.074 mol of a white solid intermediate 2-chloro-4-(2-naphthyl)pteridine was obtained, with a yield of 74%.
- In nitrogen gas, the intermediate 2-chloro-4-(2-naphthyl)pteridine 0.048 mol, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0360 mol of compound 21, with a yield of 75%.
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- 0.10 mol of 2-chloro-4-iodopteridine and 0.14 mol of 4-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.074 mol of a white solid intermediate 4-([1,1′-biphenyl]-4-yl)-2-pteridine was obtained, with a yield of 74%.
- In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-4-yl)-2-pteridine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.03552 mol of compound 22, with a yield of 74%.
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- 0.10 mol of 2-chloro-4-iodopteridine and 0.12 mol 3-biphenylyl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.076 mol of a white solid intermediate 4-([1,1′-biphenyl]-3-yl)-2-pteridine was obtained, with a yield of 76%.
- In nitrogen gas, 0.048 mol of the intermediate 4-([1,1′-biphenyl]-3-yl)-2-pteridine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0365 mol of compound 9, with a yield of 76%.
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- 0.10 mol of 2-chloro-4-iodopteridine and 0.14 mol of 9-phenanthryl boric acid were dissolved in 1 L of toluene. 0.15 mol of tetrakis(triphenylphosphine)palladium, 0.25 mol of potassium carbonate and 100 mL of distilled water were added under the protection of nitrogen gas. The reaction was carried out under stirring and reflux for 24 hours. After the reaction was ended, distilled water was added at normal temperature. The organic layer was collected by extraction with ethyl acetate, and then dried with anhydrous magnesium sulfate, followed by filtration. A liquid was obtained after distillation under reduced pressure, and then subjected to column chromatography. 0.076 mol of a white solid intermediate 2-chloro-4-(9-phenanthryl)pteridine was obtained, with a yield of 76%.
- In nitrogen gas, 0.048 mol of the intermediate 2-chloro-4-(9-phenanthryl)pteridine, 0.0576 mol of 13,13-dimethyl-7,13-dihydro-5H-indoloacridine, 0.0576 mol triethylamine, and tetrahydrofuran as a solvent were heated to 50° C.-70° C. After the reaction was ended, methanol was added at normal temperature, and then the produced solid was filtered off. The solid filtered off was added into and washed with distilled water and methanol. Then recrystallization was performed with dichloromethane and methanol, so as to obtain 0.0370 mol of compound 24, with a yield of 77%.
- Compounds 1-24 were synthesized by the above-mentioned Examples of reaction. The element analysis of the compounds was carried out by fast atom bombardment mass spectroscopy (FABMS) method. The results were listed in Table 2, wherein MS/FAB(M+) was the molecular weight measured by FABMS.
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TABLE 2 Compound No. Element Analysis MS/FAB (M+) 1 calculated values are C: 86.90%; H: 5.15%; N: 7.95%; 704.86 measured values are C: 86.91%; H: 5.15%; N: 7.94%; 2 calculated values are C: 88.03%; H: 5.01%; N: 6.96%; 804.98 measured values are C: 88.02%; H: 5.00%; N: 6.98%; 3 calculated values are C: 88.03%; H: 5.01%; N: 6.96%; 804.98 measured values are C: 88.05%; H: 5.02%; N: 6.93%; 4 calculated values are C: 88.29%; H: 5.17%; N: 6.54%; 857.05 measured values are C: 88.30%; H: 5.18%; N: 6.52%; 5 calculated values are C: 88.29%; H: 5.17%; N: 6.54%; 857.05 measured values are C: 88.28%; H: 5.16%; N: 6.56%; 6 calculated values are C: 88.91%; H: 4.90%; N: 6.19%; 905.09 measured values are C: 88.90%; H: 4.90%; N: 6.20%; 7 calculated values are C: 83.26%; H: 4.85%; N: 11.89%; 706.83 measured values are C: 83.26%; H: 4.86%; N: 11.88%; 8 calculated values are C: 84.84%; H: 4.75%; N: 10.41%; 806.95 measured values are C: 84.86%; H: 4.76%; N: 10.38%; 9 calculated values are C: 84.84%; H: 4.75%; N: 10.41%; 806.95 measured values are C: 84.83%; H: 4.76%; N: 10.41%; 10 calculated values are C: 85.29%; H: 4.93%; N: 9.78%; 859.03 measured values are C: 85.29%; H: 4.92%; N: 9.79%; 11 calculated values are C: 85.29%; H: 4.93%; N: 9.78%; 859.03 measured values are C: 85.30%; H: 4.93%; N: 9.77%; 12 calculated values are C: 86.07%; H: 4.67%; N: 9.27%; 907.07 measured values are C: 86.05%; H: 4.66%; N: 9.30%; 13 calculated values are C: 79.64%; H: 4.55%; N: 15.81%; 708.81 measured values are C: 79.66%; H: 4.55%; N: 15.79%; 14 calculated values are C: 81.66%; H: 4.49%; N: 13.85%; 808.93 measured values are C: 81.65%; H: 4.50%; N: 13.85%; 15 calculated values are C: 81.66%; H: 4.49%; N: 13.85%; 808.93 measured values are C: 81.65%; H: 4.48%; N: 13.87%; 16 calculated values are C: 82.30%; H: 4.68%; N: 13.01%; 861.00 measured values are C: 82.30%; H: 4.69%; N: 13.00%; 17 calculated values are C: 82.30%; H: 4.68%; N: 13.01%; 861.00 measured values are C: 82.32%; H: 4.68%; N: 12.99%; 18 calculated values are C: 83.24%; H: 4.44%; N: 12.33%; 909.05 measured values are C: 83.25%; H: 4.45%; N: 12.31%; 19 calculated values are C: 76.04%; H: 4.25%; N: 19.71%; 710.79 measured values are C: 76.05%; H: 4.25%; N: 19.70%; 20 calculated values are C: 78.50%; H: 4.23%; N: 17.27%; 810.90 measured values are C: 78.51%; H: 4.24%; N: 17.25%; 21 calculated values are C: 78.50%; H: 4.23%; N: 17.27%; 810.90 measured values are C: 78.50%; H: 4.21%; N: 17.29%; 22 calculated values are C: 79.33%; H: 4.44%; N: 16.23%; 862.98 measured values are C: 79.32%; H: 4.46%; N: 16.22%; 23 calculated values are C: 79.33%; H: 4.44%; N: 16.23%; 862.98 measured values are C: 79.34%; H: 4.44%; N: 16.22%; 24 calculated values are C: 80.42%; H: 4.20%; N: 15.37%; 911.02 measured values are C: 80.41%; H: 4.21%; N: 15.37%; - It can be seen from the above results that the measured results are consistent with the calculated results, indicating that the produced compounds 1 to 24 are exactly the compounds (1) to (24).
- Organic electroluminescent devices were prepared by using the compounds 1-24 prepared from the above preparation examples, and then compared with the comparative sample. In the organic electroluminescent devices, the compound of formula (I) can be used as a red phosphorescence host material, a hole-injecting material or a hole-transporting material. The disclosure was illustrated below by using the compound as a red phosphorescence host material.
- An organic electroluminescent device having the following structure was prepared by using a compound of chemical formula a as a luminescent host material, a compound of chemical formula b as a doping material, 2-TNATA (4,4,4-tri(N-naphthyl)-N-phenylamino)-triphenylamine) represented by chemical formula c as a hole-injecting material, and α-NPD (N,N′-di(naphthyl)-N,N′-diphenylbenzidine) represented by chemical formula d as a hole-transporting material:
-
ITO/2-TNATA(80 nm)/α-NPD(30 nm)/compound a+compound b(30 nm, content of b therein being 8%)/Alq3(30 nm)/LiF(0.5 nm)/Al(60 nm). - A 15Ω/cm2 (1000 Å) ITO glass substrate from Corning Co. was cut into a size of 50 mm*50 mm*0.7 mm, and then under the irradiation of microwave, washed in acetone, isopropanol, purified water in turn for 15 minutes respectively, and then further washed in UV for 30 minutes. A hole injection layer was formed by vacuum depositing 2-TNATA to a thickness of 80 nm on the substrate. A hole transport layer was formed by vacuum depositing α-NPD to a thickness of 30 nm on the hole injection layer. A light-emitting layer was formed by vacuum depositing a compound represented by chemical formula a and a compound represented by chemical formula b (at a doping ratio of 8%) to a thickness of 30 nm on the hole transport layer. An electron transport layer was formed by vacuum depositing Alg3 to a thickness of 30 nm on the light-emitting layer. On the electron transport layer, 0.5 nm LiF (electron injection) and 60 nm Al were vacuum depositing in turn, thereby an organic luminescent device was produced. In this comparative example 1 and the following application examples 1 to 24, vacuum deposition was carried out by using an EL deposition machine manufactured by DOV Co., Korean.
- The organic luminescent devices having following structures were produced by using the process in comparative example 1, with the exception that the compounds 1 to 24 shown in the preparation examples were used as the light-emitting layer compound instead of the compound a. The organic luminescent devices having the structure of ITO/2-TNATA (80 nm)/α-NPD (30 nm)/indoloacridine-containing derivatives 1 to 24+compound b] (25 nm, content of b therein being 8.0%)/Alq3(30 nm)/LiF(0.5 nm)/Al(60 nm).
- The comparative sample and the samples 1 to 24 were tested for evaluating the driving voltage, luminance, luminous efficiency and luminous color by using Keithley 2400 series digital source apparatus from the Taiwan Branch of American Keithley Instruments Inc., konica minolta CS-2000 from Konica Minolta, and CS-2000A photometer. The comparative sample and the samples 1 to 24 were subjected to the same tests. The results were listed in Table 3:
-
TABLE 3 Wavelength Driving Luminous of Compound Doping voltage Luminance efficiency luminescence No Host material material [V] [cd/m2] [cd/A] [nm] Com. Ex. 1 a b 9.8 667 6.6 636 1 1 b 8.2 829 8.1 632 2 2 b 7.5 820 8.2 636 3 3 b 7.6 765 7.6 640 4 4 b 7.2 789 7.8 636 5 5 b 8.7 838 8.2 640 6 6 b 8.5 872 8.7 640 7 7 b 8.2 901 9.1 636 8 8 b 8.6 922 9.0 632 9 9 b 8.8 938 8.9 632 10 10 b 8.0 901 9.1 640 11 11 b 8.0 886 8.5 636 12 12 b 7.9 847 8.6 636 13 13 b 7.7 835 8.6 636 14 14 b 8.6 898 8.8 632 15 15 b 8.3 847 8.5 632 16 16 b 8.0 852 8.5 640 17 17 b 7.8 809 8.4 640 18 18 b 8.3 843 8.4 640 19 19 b 8.8 935 9.1 636 20 20 b 7.7 944 9.0 632 21 21 b 7.9 920 9.3 640 22 22 b 8.3 875 8.9 636 23 23 b 7.6 836 8.6 632 24 24 b 8.2 842 8.4 640 - As shown in Table 3, the lights emitted from the samples mentioned above were in a wavelength range of from 632 to 640 nm, showing a color of red. As compared with the sample of the comparative example 1, the samples of the application examples 1 to 24 had significantly higher luminous efficiency.
- A lifetime testing apparatus LTS-1004AC of ENC Co. was used for the samples produced in the above-mentioned comparative example 1 and application examples 1 to 24, wherein lifetime of each sample was measured when 97% was reached by using 3000 nit as the standard. The results were shown in Table 4.
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TABLE 4 Sample No. Host compound Doping compound Lifetime [h] Com. Ex. 1 a b 72 1 1 b 160 2 2 b 158 3 3 b 195 4 4 b 110 5 5 b 118 6 6 b 99 7 7 b 100 8 8 b 178 9 9 b 148 10 10 b 170 11 11 b 135 12 12 b 136 13 13 b 199 14 14 b 186 15 15 b 177 16 16 b 165 17 17 b 99 18 18 b 166 19 19 b 115 20 20 b 111 21 21 b 96 22 22 b 103 23 23 b 108 24 24 b 101 - It can be confirmed from Table 4 that as compared with the sample of the comparative example 1, the samples of the application examples 1 to 24 have a longer luminescence lifetime.
- In addition, organic luminescent devices having a structure of ITO/2-TNATA (80 nm)+indoloacridine-containing derivatives 1 to 24/α-NPD (30 nm)/compound a (30 nm, where b content was 8%)/Alg3 (30 nm)/LiF (0.5 nm)/Al (60 nm) were prepared by using the process of comparative example 1, with the exception that the compounds 1 to 24 shown in the preparation examples were used as a hole injection material instead of the compound c. That is, these compounds 1-24 may be used as a hole-injecting material.
- Organic luminescent devices having a structure of ITO/2-TNATA (80 nm)/indoloacridine-containing derivatives 1 to 24+α-NPD (30 nm)/compound a+compound b (25 nm, where b content was 8.0%)/Alq3 (30 nm)/LiF (0.5 nm)/Al (60 nm) were prepared by using the process of comparative example 1, with the exception that the compounds 1 to 24 shown in the preparation examples, which may used as a hole-transporting material, were used for the compound for the hole transporting layer instead of the compound d.
- Although the present invention has been specifically described and illustrated by using exemplary embodiments, it should be understood that those of ordinary skill may take various changes in form and details without departing from the spirit and scope of the invention as defined by the following claims.
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